2,5-Dimethylphenylboronic acid

2,5-Dimethylphenylboronic acid Property

Melting point:

186-191 °C (lit.)

Boiling point:

305.1±52.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.70±0.58(Predicted)

form 

Solid

color 

White

BRN 

3241785

CAS DataBase Reference

85199-06-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2,5-Dimethylphenylboronic acid Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

Reactant for:• ;Friedel-Crafts alkylation1• ;Suzuki-Miyaura coupling2

Uses

suzuki reaction

Uses

Reactant for:

• Friedel-Crafts alkylation
• Suzuki-Miyaura coupling

Synthesis

The general procedure for the synthesis of 2,5-dimethylphenylboronic acid from trimethyl borate, 2,5-dimethylbromobenzene and aqueous electrophoretic grade was as follows: 1-bromo-2,5-dimethylbenzene (25.0 g, 0.135 mol) was dissolved in 200 ml of tetrahydrofuran under the protection of nitrogen in a 1 L round-bottomed flask and cooled to -78 °C. A 1.6 M n-butyllithium solution was added slowly dropwise and the reaction was stirred for 2 hours keeping the temperature at -78 °C. Subsequently, trimethyl borate (18.2 g, 0.176 mol) was added dropwise and the reaction continued at the same temperature. After completion of the reaction, 1 equivalent of hydrochloric acid (101 ml, 0.162 mol) was added to acidify the reaction mixture at room temperature and stirred for 1 hour. The reaction solution was concentrated under reduced pressure and the resulting solid was recrystallized from hexane to give Intermediate 1-b (12.5 g, 62% yield).

References

[1] Patent: KR2015/52989, 2015, A. Location in patent: Paragraph 0326-0331